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Concept
Aldol reaction
Summary
The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound.
These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones.
Aldol structural units are found in many important molecules, whether naturally occurring or synthetic. The aldol reaction is a common means of forming carbon–carbon bonds in organic chemistry.
The reaction is used in several industrial syntheses, notably of pentaerythritol, trimethylolpropane, the plasticizer 2-ethylhexanol, and the drug Lipitor (atorvastatin, calcium salt). For many of the commodity applications, the stereochemistry of the aldol reaction is unimportant, but the topic is of intense interest for the synthesis of many specialty chemicals.
The aldol reaction unites two relatively simple molecules into a more complex one. Increased complexity arises because up to two new stereogenic centers (on the α- and β-carbon of the aldol adduct, marked with asterisks in the scheme below) are formed. Modern methodology is capable of not only allowing aldol reactions to proceed in high yield but also controlling both the relative and absolute configuration of these stereocenters. This ability to selectively synthesize a particular stereoisomer is significant because stereoisomers can have distinctive chemical and biological properties.
For example, stereogenic aldol units are especially common in polyketides, a class of molecules found in biological organisms. In nature, polyketides are synthesized by enzymes that effect iterative Claisen condensations. The 1,3-dicarbonyl products of these reactions can then be variously derivatized to produce a wide variety of interesting structures. Often, such derivitization involves the reduction of one of the carbonyl groups, producing the aldol subunit.
Official source
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